It’s Lonely Being a Single Founder

As a single founder, I felt like I was carrying a weight that I couldn’t share with anyone. Here’s how I’m fighting back…

“Are you sure you have what it takes?”

“Your chances of success would certainly be higher if you had someone technical leading the charge.”

“To be completely honest, I don’t really know if you can handle this on your own.”

“Maybe you should quit now.”

The objections and criticisms flew, and there was nothing I could say to shut them up.

After all, I was dealing with something that people much smarter and more successful have failed to beat; I was trying to quiet the voices in my own head.

I can’t remember connecting with any line so deeply as when Jonathan Hefter told Alyson Shontell that “starting [his company] as a sole founder was the most isolating experience of my life.”

My goal here is not to write a whiny post complaining about my lot in life. All things considered, I have it really damn good.

But the issues and challenges of being a single founder are unique to the job, and they can absolutely derail your business.

I hope that by writing about it, I can help other founders going through the same thing battle through this crippling obstacle and come out stronger on the other side.

The Loneliness of Being a Single Founder

I’m not a “lonely” person as some might traditionally think of the term.

I’m happily engaged.

I have amazing, fulfilling, deep friendships with people that I love and care about very much.

But single founder loneliness is solitude unlike any other.

Solitude

Every responsibility and every failure is yours.

I’m surrounded by brilliant, motivated, hard-working people at Groove.

Every single day, we work really hard together on building this business and helping our customers be successful.

I help wherever I can, but our team does a lot of things that I can’t or don’t know how to do.

But at the end of the day, if there’s a failure in the chain, I’m responsible.

I made the decision about who should handle which tasks.

I’m the one the customer is angry at for something going wrong.

Ultimately, it’s my fault.

On an even more painful level, if the business fails and my employees lose their income…

That’s 100% my fault.

It’s one of my biggest fears as a founder, and while it gets easier as the business grows more successful, it never truly goes away.

At my last company, we had four co-founders. While none of us wanted the business to fail, there was at least some comfort in knowing that there were always three others bearing — and talking about — that same burden.

There’s literally nobody else in the world who bears that same exact responsibility for your team as you, the lone founder.

That’s an incredibly isolating feeling.

Four Ways to Beat Single Founder Loneliness

I don’t have all of the answers yet.

It’s a challenge I still struggle with at times.

But I’m feeling massively better about being a single founder now than I was six months ago, when every day felt like I was sitting alone on an island with no escape.

Here’s how I changed that:

1) I Realized That in Some Ways, I’m Not Alone.

For too long, I made the mistake of thinking that because nobody in my life related exactly to what I was going through, they wouldn’t understand.

But when I actually tried talking to a friend about it over lunch, I was shocked at how relieved I felt afterwards.

How simply getting the words — “this fucking sucks, man” — out and into the ears of a supportive, comforting person instantly lightened the load.

He’s never been a founder. He’s never worn those shoes.

But he listened, and he told me that things would be fine.

It doesn’t matter if that’s a lie. It helped.

My friends and family come to me for support with problems I may never relate to: medical problems, job challenges, other personal issues.

I’m always happy to lend an ear, and in almost every situation, I can tell that the other person feels better after we talked.

I have no idea why I was scared to do the same.

Now, when I’m feeling particularly overwhelmed, I make it a point to take time out of my day and have lunch with a friend, or talk about it over dinner with my fiancee.

And it always helps.

Takeaway: Just like any other problem, talking to someone about it can be super helpful. As I learned, it doesn’t matter if that person doesn’t know exactly what you’re going through. Just talk.

2) I Disconnected

One of the things that made founder loneliness worse was being constantly confronted with it.

I’d get emails, support requests and Tweets that were prominent reminders of decisions and responsibilities that only I had to deal with.

When I’m working, that’s fine. It’s part of the job I signed up for.

But when it bleeds into the rest of my life, it’s a constant source of anxiety.

I tried a lot of things: meditating, taking long walks, “forcing” myself not to think about things.

But in reality, the only thing that truly worked for “disconnecting” was, quite literally, disconnecting.

I began turning off push notifications on my phone in the evenings.

If I was doing anything on the computer unrelated to Groove, I’d close my email client.

I stopped checking Twitter “just because.”

Disconnected

On the whole, those 3-5 hours of being totally disconnected every night have been one of the biggest breakthroughs in battling not just single founder stress, but any stress altogether.

Takeaway: You can do whatever helps you disconnect from your work, as long as you do something. For me, that meant turning off every reminder of Groove for a few hours a day.

3) I Started Taking Better Care of Myself.

Perhaps the most obvious — and most-often repeated — way to battle loneliness and anxiety is by getting healthier.

The problem is that “getting healthier” is absurdly vague. Where do you start?

And a Google search for “get healthier” yields millions of tips and solutions that are enough to overwhelm anyone.

Overwhelming

For me, the mindset of “well if I want to be healthy, I need to exercise five times a week for the rest of my life” causes as much anxiety as what I was trying to cure in the first place.

So I started small.

I exercised once per week for a while.

That made it easier to step up to two.

And three.

Now, I look forward to my workouts, because I know that they’re helping me battle stress and making me happier.

In a similar vein, I began to stand instead of sitting.

I bought a standing desk, and started using it for an hour each day.

And then two hours.

And three hours.

Now, I spend about half of my day standing up, my back feels much better, and I don’t get into the same desk “slump” I would find myself in after being slouched over for ten hours straight.

Standing Desk

These aren’t huge-scale health changes. They were tiny steps I took to improve my wellbeing, and even those small changes made a big impact on dealing with my founder loneliness.

Takeaway: Whether you’re a founder or not, getting healthier can go a long way toward helping you deal with your stress. And it doesn’t take changing your whole life. Start small, and the results will motivate you.

4) I Practice Openness With the Team.

Around the time we started this blog — an exercise in transparency with our audience — we began to be more open and transparent internally, too.

On our weekly call, I make an effort to bring our team in on the state of the business; where it’s going, how we’re doing, how far we are from breakeven, things like that.

I ask for feedback.

And then I act on it.

We’ve recently been automating this process with 15five, and it’s brought a lot of great changes to the business.

15five

Having great people around me that have the ability, knowledge and willingness to offer feedback — brutal, honest insights — is hugely valuable.

And when I am feeling stressed about a choice I have to make, I talk to them about it.

To date, nothing bad has ever happened from asking the team to weigh in on founder-level decisions.

It brings us closer together, makes everyone happier and more invested in the business, and on a personal level, it makes me feel like I don’t sit on an island.

Takeaway: Being open and honest with your employees can go a long way in making you feel less isolated. And it has massive benefits for the team and your business, too. There’s a whole lot less that you “can’t” share than you probably think.

We’re All in This Together

Single founder loneliness sucks.

There’s no doubt about it, and there’s no way to avoid it altogether.

But hopefully my experiences can help you deal with it better.

To not be afraid to talk to people about your problems, like I was.

To not constantly be surrounded with reminders of the loneliness, like I was.

To not ignore the loneliness-crushing benefits of healthy habits, like I was.

And if you can’t think of anyone you’d want to share your burden with, then just share it below in the comments. We’ll all help each other.